ETHYNYL P-TOLYL SULFONE
- Product Name
- ETHYNYL P-TOLYL SULFONE
- CAS No.
- 13894-21-8
- Chemical Name
- ETHYNYL P-TOLYL SULFONE
- Synonyms
- 1-(ethynylsulfonyl)-4-Methylbenzene;TOSYLACETYLENE;ETHYNYL P-TOLYL SULFONE;Ethynylp-TolylSulfone>p-tolylsulfonylacetylene;4-(Ethynylsulfonyl)toluene;P-TOLUENESULFONYLACETYLENE;Ethynyl p-Tolyl Sulfone;Benzene, 1-(ethynylsulfonyl)-4-methyl-;p-Toluenesulfonylacetylene, Tosylacetylene
- CBNumber
- CB3427572
- Molecular Formula
- C9H8O2S
- Formula Weight
- 180.22
- MOL File
- 13894-21-8.mol
ETHYNYL P-TOLYL SULFONE Property
- Melting point:
- 73-74 °C (lit.)
- Boiling point:
- 297.9±33.0 °C(Predicted)
- Density
- 1.219±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- organic solvents: soluble(lit.)
- form
- powder to crystal
- color
- White to Light yellow
- BRN
- 2556169
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 419869
- Product name
- Ethynyl p-tolyl sulfone
- Purity
- 98%
- Packaging
- 1g
- Price
- $110
- Updated
- 2024/03/01
- Product number
- E0466
- Product name
- Ethynyl p-Tolyl Sulfone
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $172
- Updated
- 2024/03/01
- Product number
- E0466
- Product name
- Ethynyl p-Tolyl Sulfone
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $547
- Updated
- 2024/03/01
- Product number
- E938863
- Product name
- Ethynyl p-Tolyl Sulfone
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 7929AL
- Product name
- Ethynyl p-Tolyl Sulfone
- Packaging
- 5g
- Price
- $343
- Updated
- 2021/12/16
ETHYNYL P-TOLYL SULFONE Chemical Properties,Usage,Production
Uses
Ethynyl p-tolyl sulfone (Tosylacetylene) may be used in the synthesis of 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) protected derivatives. It may be used as starting reagent for the synthesis of optically active indan-2-ols.
Application
Ethynyl p-Tolyl Sulfone is a dienophile used in electrocyclic reactions such as dipolar cycloaddition, Diels-Alder reaction, and ene cyclization; electron-poor Michael acceptor in conjugate additions; undergoes direct displacement with organometallic complexes to give aryl- or alkylacetylenes.
Preparation
Ethynyl p-Tolyl Sulfone has been prepared by several groups over the years employing a variety of synthetic
strategies including ethynyl Grignard addition to p-toluenesulfonyl fluoride, dehydroiodination of (E)-2-iodo-1-
tosyl-1-ethene, oxidative elimination of β-[(4-methylphenyl)seleno]vinyl sulfone, dehydrobromination of cis-and trans-2-bromovinyl 4-methylphenyl sulfone,23 diazotization of 4-[(4-methylphenyl)sulfonyl]-5-
aminoisoxazole, and oxidation of ethynyl thioether. The modified strategy commonly used today is an
established Friedel-Crafts based procedure first performed by Bhattacharya et al. but recently exploited by
Waykole and Paquette (eq 1). Its simplicity and mildness has shown it to be broadly useful since it bypasses
the need for immoderate conditions encountered in the earlier strategies.
Synthesis Reference(s)
The Journal of Organic Chemistry, 57, p. 697, 1992 DOI: 10.1021/jo00028a053
storage
Decomposition of the intermediate complex p-toluenesulfonyl chloride-aluminum chloride-bis(trimethylsilyl)acetylene with hydrochloric acid and ice is exothermic and due caution is recommended. Also, a nitrogen atmosphere is suggested throughout its preparation due to the hygroscopic nature of the reagents and intermediate(s) involved.
Purification Methods
Recrystallise the sulfone from pet ether, *C6H6 or EtOH (m 66o), and dry it in a vacuum. [Beilstein 6 III 1397, 6 IV 2160.]
ETHYNYL P-TOLYL SULFONE Preparation Products And Raw materials
Raw materials
Preparation Products
ETHYNYL P-TOLYL SULFONE Suppliers
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